1. Casino Night (Season 2, Episode 22)
“I’m in love with you.”
“Casino Night” moved the saga of Jim and Pam forward in an unexpected and heartbreaking way. Naturally, this episode registers as a standout. After possibly the finest ‘will they, won’t they’ ever concocted on television, Jim finally confesses his love to Pam. They share a kiss, and then another. The only shame is that those last moments often overshadow a genuinely hilarious episode that sees Michael throwing a very fancy — and very illegal — night of gambling in the warehouse while trying to split time between Jan and his realtor, Carol.
Image Source: Basement Rejects